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Séminaire Chimie ED459

Heavy cyclobutadienes and heavy ketones

Prof. Tsukasa Matsuo (Department of Applied Chemistry, Faculty of Science and Engineering, Kindai University, Osaka, Japan)

publié le , mis à jour le

Le Jeudi 15 Novembre 2018 à 14h
Institut Européen des Membranes, salle de conférences (campus Balard Bât. 40, 300 avenue Émile-Jeanbrau)

In 2011, we reported the synthesis of the first cyclobutadiene (CBD) silicon analogue, Si4(EMind)4, supported by the fused-ring bulky EMind groups (EMind = 1,1,7,7-tetraethyl-3,3,5,5-tetramethyl-s-hydrindacen-4-yl). The Si4 ring shows a planar rhombic charge-separated structure as a consequence of the polar Jahn-Teller (J-T) distortion to counteract the antiaromaticity with a cyclic 4π-electron system. This result is in sharp contrast to the fact that the carbon CBDs are mainly stabilized by the covalent J-T distortion producing a rectangular-shaped C4 ring with two isolated C=C double bonds. In 2018, we reported the CBD germanium analogue, Ge4(EMind)4, which can be obtained as room-temperature stable dark red crystals via the reaction of the 1,2-dichlorodigermene with lithium naphthalenide. The 4π-electron antiaromaticity is also stabilized by the polar J-T distortion in the Ge4 ring producing a planar diamond-like charge-separated structure. The heavy ketones including a germanone, (Eind)2Ge=O (Eind = 1,1,3,3,5,5,7,7-octaethyl-s-hydrindacen-4-yl), with a planar tricoordinate Ge atom and a terminal oxygen atom will also be presented.

Contact local ICGM : Michel Wong Chi Man, D.R. CNRS (équipe AM2N)


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